In the Caribbean, chic, affordable stays are becoming as common as powdery sands, swaying palm trees and crystal blue waters.
Samana Peninsula, Dominican Republic
With a fleet of ritzy hotels crowding its shores, this pristine Caribbean island sports a pricey facade. But there are plenty of deals — if you know where to look. The Samana Peninsula, a strip of sand between Punta Cana and Puerto Plata, is the antithesis of the big-ticket resort towns. Book a room at The Bannister Hotel ($152 per night), which includes three top-notch restaurants, an infinity pool, a 3,500-square-foot spa and two tennis courts. Spend your days relaxing on the beach, horseback riding in the mountains ($20 to $80 depending on your bartering skills) or hiking to the 120-foot El Limon waterfall. JS Tip: Go between January and mid-March, and you'll spot hundreds of humpback whales migrating in Samana Bay.
Postcard-perfect sands, a soulful vibe and easy access make Jamaica the ideal weekend getaway. Head to Negril on the west side, where the black-streaked favorite Treasure Beach is set among a patchwork of rolling farmland. Although you may be tempted to splurge on a five-star pad like The Caves or Rockhouse Hotel, opt for a boho-chic cottage at Jake's ($98 per night). Here, you'll save big on mouthwatering local fare and blissed-out beach time. Tuck into open-fire jerk chicken ($6.50) with a side of live reggae at 3 Dives or cruise a mile off the coast to Floyd's Pelican Bar, a floating shack made of driftwood and palms. Then while away your days next to the crystal-clear water at Seven Mile beach with a Red Stripe in hand.
Despite its high-profile clientele and preppy sailing scene, Antigua has plenty of stylish, low-key resorts. We love the all-inclusive rooms at Blue Waters ($188 per night) — think premium alcoholic drinks (no Bud Light in sight), three infinity pools, free kayaking and an unbeatable location on a private bay. Bonus: Non-stop airfare can drop as low as $280 round-trip. Cha-ching!
Want to live out your Castaway fantasies? Look no further than St. Lucia's tropical wilderness. Check into the Hummingbird Beach Resort, a tranquil retreat just north of Soufriere, for only $213 a night. Then hire a guide ($28) or go rogue on a hike up The Pitons, the island's two towering peaks — take the Tet Paul Nature Trail for panoramic Atlantic and Caribbean views. Rest those sore muscles with a mud bath at Sulfur Springs Park ($5 admission) followed by a day lounging at Anse Chastanet, a natural black sand beach and prime snorkel spot. In the evening, treat yourself to dinner at Ladera Resort's Dasheene Restaurant. At 1,100 feet up, its terrace has jaw-dropping vistas of Petit Piton complemented by chef Orlando Satchell's locally sourced farm-to-table fare (pepper-marinated grilled shrimp, rack of lamb spiced with cacao and coconut sauce).
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Puerto Rico is full of affordable hideways ⎯ and airfare tends to be much cheaper than other islands. To experience the best of the east and west, we recommend you split your time between San Juan and Rincón. Dig into old town San Juan's local foodie scene at low-key restaurants like Deaverdura, which serves tostones (fried plantain slices) and traditional pasteles with rice and beans — for a wallet-friendly $8. Or, eat your way through the farmer's market at Plaza Ventana del Mar, in the Condado neighborhood. Here you'll find bacalaitos (fried cod fritters), alcapurrias and artisanal empanadas, all for under $10 each. Then road trip (3 hours) to Rincón on the west coast where you can stay at the charming Blue Boy Inn (from $165) and hang ten with the surfers. The ocean is free after all.
Most tourists head for Tobago, but you'll get the most bang for your buck along with a killer art scene and cheap eats in Trinidad (about 95 percent of the population lives here). Book a bungalow at Acajou (starting at $160), on the north coast and spend an afternoon lounging in a hammock with views of the river and ocean. Or see colorful works by Peter Doig, Chris Ofili and more local artists at galleries like 101, Horizons and The National Museum. Refuel with heaping plates of roti, doubles (chickpea pockets), curried crab and dumplings from the street food carts, or hit Richard's Shark & Bake stand for fried shark seafood rolls topped with tamarind hot sauce and coleslaw. When it turns dark, take a $60 bioluminescent paddle board tour, a steal compared to Puerto Rico's $120 excursion.
Searching for powdery beaches, a charming capital city and some of the best diving in the world? This Dutch Caribbean island is it. Check into the Avila Hotel (from $250) on the southern coast and just a short walk from Willemstad. The city's colorful 17th- and 18th-century Dutch Colonial buildings, a UNESCO World Heritage site, are one of the Caribbean's most photographed scenes. For authentic bites, head to the Floating Market in downtown Willemstad, where locals pull up boats overflowing with fresh produce along the canal sidewalk, or grab lunch at the Old Market.